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Polyacrylates containing primary amino groups

Assignee: Czech Academy of Sciences
•
Filing: 1976-11-29
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Granted: 1978-02-28
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Expires: 1996-11-29
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Abstract

Abstract A polymeric material containing primary amino groups is prepared by copolymerizing an acylaminophenoxy acrylate or methacrylate with a hydroxyalkyl ester or an amide of acrylic or methacrylic acid, and treating the resulting copolymeric material with a hydrolytic agent to convert the acylamino groups into primary amino groups. Such monomeric materials may also be copolymerized with a crosslinking agent comprising an ester or an amide containing two or more acryloyl or methacryloyl groups.

Inventors

  • 👤 Otto Wichterle
  • 👤 Jiri Coupek

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 16:15
CPC Classifications
C; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F8/00

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 164 words
A method of producing a polymeric material containing primary amino groups, which comprises copolymerizing (a) a monomer having the general formula: ##STR2## wherein R 1 is selected from the group consisting of H and CH 3 , Ar is a bifunctional aromatic residue, R 2 is an acyl group, and x is 1 to 20, and (b) an amount of a comonomer which is 2 to 30 times greater than the amount of said monomer by weight, said comonomer being selected from the group consisting of a hydroxyalkyl ester of acrylic acid, a hydroxyalkyl ester of methacrylic acid, an amide of acrylic acid, an amide of methacrylic acid, and styrene, the copolymerization being conducted at a temperature of 60° to 90° C; and treating the resulting copolymeric material at a temperature of 75° - 100° C. with a hydrolytic agent selected from the group consisting of a strong mineral acid and a strong mineral base to convert the acylamino groups into primary amino groups.
Claim 2
Independent Claim 164 words
A method of producing a polymeric material containing primary amino groups, which comprises copolymerizing (a) a monomer having the general formula: ##STR2## wherein R 1 is selected from the group consisting of H and CH 3 , Ar is a bifunctional aromatic residue, R 2 is an acyl group, and x is 1 to 20, and (b) an amount of a comonomer which is 2 to 30 times greater than the amount of said monomer by weight, said comonomer being selected from the group consisting of a hydroxyalkyl ester of acrylic acid, a hydroxyalkyl ester of methacrylic acid, an amide of acrylic acid, an amide of methacrylic acid, and styrene, the copolymerization being conducted at a temperature of 60° to 90° C; and treating the resulting copolymeric material at a temperature of 75° - 100° C. with a hydrolytic agent selected from the group consisting of a strong mineral acid and a strong mineral base to convert the acylamino groups into primary amino groups.
Claim 3
Dependent Claim 15 words
A method according to claim 1, in which the bifunctional aromatic residue is phenylene group.
Claim 4
Dependent Claim 14 words
A method according to claim 1, in which R 2 is an acetyl group.
Claim 5
Dependent Claim 14 words
A method according to claim 1, in which R 2 is a benzoyl group.
Claim 6
Dependent Claim 33 words
A method according to claim 1, in which the comonomer is a hydroxyalkyl ester selected from the group consisting of a hydroxyalkyl ester of acrylic acid and a hydroxyalkyl ester of methacrylic acid.
Claim 7
Dependent Claim 30 words
A method according to claim 1, in which the comonomer is an amide selected from the group consisting of an amide of acrylic acid and an amide of methacrylic acid.
Claim 8
Independent Claim 226 words
A method of producing a polymeric material containing primary amino groups, which comprises copolymerizing (a) a monomer having the general formula: ##STR3## wherein R 1 is selected from the group consisting of H and CH 3 , Ar is a bifunctional aromatic residue, R 2 is an acyl group, and x is 1 to 20, (b) an amount of a comonomer which is 2 to 30 times greater than the amount of said monomer by weight, said comonomer being selected from the group consisting of a hydroxyalkyl ester of acrylic acid, a hydroxyalkyl ester of methacrylic acid, an amide of acrylic acid, an amide of methacrylic acid, and styrene, and (c) up to 70% by weight, based on the total weight of said monomer and said comonomer, of a crosslinking agent selected from the group consisting of an ester containing at least two acryloyl groups, an ester containing at least two methacryloyl groups, an amide containing at least two acryloyl groups, an amide containing at least two methacryloyl groups, and divinyl benzene, the copolymerization being conducted at a temperature of 60° to 90° C.; and treating the resulting copolymeric material at a temperature of 75° - 100° C. with a hydrolytic agent selected from the group consisting of a strong mineral acid and a strong mineral base to convert the acylamino groups into primary amino groups.
Claim 9
Independent Claim 226 words
A method of producing a polymeric material containing primary amino groups, which comprises copolymerizing (a) a monomer having the general formula: ##STR3## wherein R 1 is selected from the group consisting of H and CH 3 , Ar is a bifunctional aromatic residue, R 2 is an acyl group, and x is 1 to 20, (b) an amount of a comonomer which is 2 to 30 times greater than the amount of said monomer by weight, said comonomer being selected from the group consisting of a hydroxyalkyl ester of acrylic acid, a hydroxyalkyl ester of methacrylic acid, an amide of acrylic acid, an amide of methacrylic acid, and styrene, and (c) up to 70% by weight, based on the total weight of said monomer and said comonomer, of a crosslinking agent selected from the group consisting of an ester containing at least two acryloyl groups, an ester containing at least two methacryloyl groups, an amide containing at least two acryloyl groups, an amide containing at least two methacryloyl groups, and divinyl benzene, the copolymerization being conducted at a temperature of 60° to 90° C.; and treating the resulting copolymeric material at a temperature of 75° - 100° C. with a hydrolytic agent selected from the group consisting of a strong mineral acid and a strong mineral base to convert the acylamino groups into primary amino groups.
Claim 10
Dependent Claim 28 words
A method according to claim 7, in which the copolymerization is carried out in the presence of an organic solvent in which the resulting copolymeric material is soluble.
Claim 11
Dependent Claim 28 words
A method according to claim 7, in which the copolymerization is carried out in the presence of an organic solvent from which the resulting copolymeric material is precipitated.
Claim 12
Dependent Claim 21 words
A method according to claim 7, in which the copolymerization is carried out in suspension form in the presence of water.
Claim 13
Dependent Claim 16 words
A method according to claim 7, in which the bifunctional aromatic residue is a phenylene group.
Claim 14
Dependent Claim 14 words
A method according to claim 7, in which R 2 is an acetyl group.
Claim 15
Dependent Claim 14 words
A method according to claim 7, in which R 2 is a benzoyl group.
Claim 16
Dependent Claim 33 words
A method according to claim 7, in which the comonomer is a hydroxyalkyl ester selected from the group consisting of a hydroxyalkyl ester of acrylic acid and a hydroxyalkyl ester of methacrylic acid.
Claim 17
Dependent Claim 30 words
A method according to claim 7, in which the comonomer is an amide selected from the group consisting of an amide of acrylic acid and an amide of methacrylic acid.
Claim 18
Independent Claim 147 words
A method of producing a polymeric material containing primary amino groups, which comprises copolymerizing at a temperature of 60° to 90° C. (a) an aminoacrylate selected from the group consisting of 2-(p-acetaminophenoxy)-ethyl methacrylate and 2-(p-acetaminophenoxy)-ethyl acrylate, (b) an amount of a hydroxy-acrylate which is 2 to 30 times greater than the amount of said aminoacrylate by weight, said hydroxy-acrylate being selected from the group consisting of 2-hydroxyethyl methacrylate and 2-hydroxyethyl acrylate, and (c) up to 70% by weight, based on the total weight of said aminoacrylate and said hydroxy-acrylate, of a crosslinking agent selected from the group consisting of ethylene dimethacrylate and ethylene diacrylate; and treating the resulting copolymeric material at a temperature of 75° - 100° C. with a hydrolytic agent selected from the group consisting of a strong mineral acid and a strong mineral base to convert the indicated acetamino groups into primary amino groups.
Claim 19
Independent Claim 147 words
A method of producing a polymeric material containing primary amino groups, which comprises copolymerizing at a temperature of 60° to 90° C. (a) an aminoacrylate selected from the group consisting of 2-(p-acetaminophenoxy)-ethyl methacrylate and 2-(p-acetaminophenoxy)-ethyl acrylate, (b) an amount of a hydroxy-acrylate which is 2 to 30 times greater than the amount of said aminoacrylate by weight, said hydroxy-acrylate being selected from the group consisting of 2-hydroxyethyl methacrylate and 2-hydroxyethyl acrylate, and (c) up to 70% by weight, based on the total weight of said aminoacrylate and said hydroxy-acrylate, of a crosslinking agent selected from the group consisting of ethylene dimethacrylate and ethylene diacrylate; and treating the resulting copolymeric material at a temperature of 75° - 100° C. with a hydrolytic agent selected from the group consisting of a strong mineral acid and a strong mineral base to convert the indicated acetamino groups into primary amino groups.
Claim 20
Independent Claim 90 words
A method of producing a polymeric material containing primary amino groups, which comprises copolymerizing at a temperature of 60° to 90° C. 2-(p-acetaminophenoxy)-ethyl methacrylate, an amount of 2-hydroxyethyl methacrylate which is 2 to 30 times greater than the amount of said aminomethacrylate by weight, and up to 70% by weight based on the total weight of said aminomethacrylate and said hydroxy-methacrylate, of ethylene dimethacrylate; and treating the resulting copolymeric material at a temperature of 75° - 100° C. with hydrochloric acid to convert the acetamino groups into primary amino groups.
Claim 21
Independent Claim 90 words
A method of producing a polymeric material containing primary amino groups, which comprises copolymerizing at a temperature of 60° to 90° C. 2-(p-acetaminophenoxy)-ethyl methacrylate, an amount of 2-hydroxyethyl methacrylate which is 2 to 30 times greater than the amount of said aminomethacrylate by weight, and up to 70% by weight based on the total weight of said aminomethacrylate and said hydroxy-methacrylate, of ethylene dimethacrylate; and treating the resulting copolymeric material at a temperature of 75° - 100° C. with hydrochloric acid to convert the acetamino groups into primary amino groups.
Claim 22
Dependent Claim 15 words
A polymeric material containing primary amino groups, produced by the method according to claim 1.
Claim 23
Dependent Claim 15 words
A polymeric material containing primary amino groups, produced by the method according to claim 7.

References Cited (Backward Citations)

US3425988A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-02-27 1981-08-29 1982-02-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-02-27 1985-08-29 1986-02-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-02-27 1989-08-29 1990-02-28 $7700.00 Window Closed / Lapsed

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